CN111039970A - Pyridyl boron dipyrromethene derivative dye ligand and preparation method thereof - Google Patents
Pyridyl boron dipyrromethene derivative dye ligand and preparation method thereof Download PDFInfo
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- CN111039970A CN111039970A CN201911420103.2A CN201911420103A CN111039970A CN 111039970 A CN111039970 A CN 111039970A CN 201911420103 A CN201911420103 A CN 201911420103A CN 111039970 A CN111039970 A CN 111039970A
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- derivative dye
- boron dipyrromethene
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- 239000003446 ligand Substances 0.000 title claims abstract description 35
- 229910052796 boron Inorganic materials 0.000 title claims description 21
- -1 Pyridyl boron dipyrromethene derivative Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- 239000006227 byproduct Substances 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 15
- OVTCUIZCVUGJHS-UHFFFAOYSA-N dipyrrin Chemical compound C=1C=CNC=1C=C1C=CC=N1 OVTCUIZCVUGJHS-UHFFFAOYSA-N 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000004327 boric acid Substances 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 238000002390 rotary evaporation Methods 0.000 claims description 8
- 238000000967 suction filtration Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 229960001701 chloroform Drugs 0.000 claims description 4
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims description 4
- 239000002274 desiccant Substances 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000004809 thin layer chromatography Methods 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 3
- 229910052734 helium Inorganic materials 0.000 claims description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 3
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 abstract description 11
- 230000003287 optical effect Effects 0.000 abstract description 6
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 26
- 238000002189 fluorescence spectrum Methods 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 6
- 230000007704 transition Effects 0.000 description 6
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000011365 complex material Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 239000012621 metal-organic framework Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- MFFMQGGZCLEMCI-UHFFFAOYSA-N 2,4-dimethyl-1h-pyrrole Chemical compound CC1=CNC(C)=C1 MFFMQGGZCLEMCI-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- PAPNRQCYSFBWDI-UHFFFAOYSA-N DMP Natural products CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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Abstract
The invention discloses a pyridyl BODIPY derivative dye ligand, which takes 1,3,5, 7-tetramethyl BODIPY as a core skeleton, and pyridine is grafted on 2,6, 8-position of the pyridyl BODIPY derivative, so as to form a novel BODIPY derivative, namely an organic dye ligand compound 2,6,8- [ 4-pyridine ] -4, 4-difluoro-1, 3,5, 7-tetramethyl-4-bora-3 a,4 a-diaza-s-indazxi with optical activity in a visible light-near infrared region, and simultaneously has excellent metal coordination capacity and pH sensitivity. The invention also discloses a preparation method of the pyridyl BODIPY derivative dye ligand, which is simple and easy to control and has universal adaptability.
Description
Technical Field
The invention relates to the field of organic dye ligand compounds, in particular to a pyridyl boron dipyrromethene derivative dye ligand and a preparation method thereof.
Background
In recent decades, the research on metal-organic framework optical functional materials has been greatly developed, and the construction of metal complex materials with photoactivity by using organic dye molecules has been the focus of material research and development. Compared with some common organic dye ligand molecules such as rhodamine, fluorescein, naphthalimide and the like, the fluorescent dye ligand of BODIPY not only ensures the excellent optical activity of the BODIPY dye molecule, such as strong visible light absorption, high molar extinction coefficient, sharp fluorescence emission, high fluorescence quantum yield and the like, because the core skeleton has the structures of boron-nitrogen six-membered rings in the same conjugate plane and pyrrole five-membered rings on two sides, but also has unique physicochemical properties such as relatively insensitivity to chemical environment change, pH value and solvent polarity, good physiological stability and the like, and is widely applied to various fields such as sensors, fluorescent probes, information storage, optoelectronic devices, solar cells, biological markers in life science and the like, however, the BODIPY molecule has the advantages of excellent photophysical stability and the like, however, the metal complex materials used to construct the photoactive structures must have good metal ion coordination capability.
Usually, functional groups with different functions are introduced into a core skeleton of the BODIPY, so that the photophysical properties of the BODIPY can be regulated, for example, a methyl functional group is introduced into the 1,3,5, 7-position to form 1,3,5, 7-tetramethyl boron dipyrromethene, so that the photophysical properties of dye molecules can be regulated, and the fluorescence quantum yield can be obviously improved; the introduction of the electron-pushing functional group and the electron-pulling functional group on the 2-position and the 6-position respectively is favorable for the dye molecules to generate red and blue shift phenomena, and the introduction of the electron-pushing functional group on the 8-position is favorable for enhancing the fluorescence emission and improving the quantum yield. The pyridyl belongs to electron-pushing functional groups, has better metal coordination capacity, and hopefully can regulate and control the photophysical property of the BODIPY dye and improve the coordination capacity to metal ions by combining the BODIPY and the pyridyl, thereby laying a good foundation for the dye ligand molecules in the construction of optical active metal-organic framework optical functional materials.
Disclosure of Invention
The invention aims to provide a pyridyl boron dipyrromethene derivative dye ligand which increases the coordination capacity to metal ions and has optical activity in a visible light-near infrared region.
The invention also aims to provide a preparation method of the pyridyl boron dipyrromethene derivative dye ligand, which is simple and easy to control and has universal adaptability.
In order to achieve the above purpose, the solution of the invention is:
a pyridyl boron dipyrromethene derivative dye ligand, the chemical structural formula of which is shown in formula I,
is named 2,6,8- [ 4-pyridine ] -4, 4-difluoro-1, 3,5, 7-tetramethyl-4-bora-3 a,4 a-diaza-s-indacene.
A preparation method of a pyridyl boron dipyrromethene derivative dye ligand comprises the following steps:
and 4, dissolving the rotary-evaporated product by using a small amount of solvent, adding water for extraction, drying the organic phase obtained by extraction by using a drying agent, filtering, carrying out rotary evaporation concentration, carrying out sectional separation by using a chromatographic column, collecting and evaporating a second-stage product by distillation, and finally obtaining red powder, namely the target compound, namely the pyridyl boron dipyrromethene derivative dye ligand.
In the step 1, the chemical structural formula of the 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-boron dipyrromethene is as follows:
the chemical structural formula of the 4-pyridine boric acid is as follows:
in the step 1, the alkali is one or two of potassium carbonate and sodium carbonate, and the palladium catalyst is one or two of [1,1' -bis (diphenylphosphino) ferrocene ] -palladium dichloride catalyst and [ tetrakis (triphenylphosphine) ] palladium catalyst; the molar ratio of the 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-fluoroboron dipyrromethene to the 4-pyridine boric acid to the alkali to the palladium catalyst is 0.50-1.00: 1.10-3.20: 1.40-2.80: 0.05-0.10.
In the step 1, the molar ratio of the 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-fluoroboron dipyrromethene to the 4-pyridine boric acid to the base to the palladium catalyst is 0.52:1.13:1.45: 0.05.
In the step 2, the protective gas is one of nitrogen, helium and argon, the reaction medium is one or more of water, dichloromethane, trichloromethane, tetrahydrofuran, dioxane, acetonitrile, DMF, toluene, ethyl acetate, n-hexane, petroleum ether, methanol, ethanol and isopropanol, the reaction temperature is 80 ℃, and the reaction time is 14 h.
In the step 2, the reaction medium is a dioxane-water mixed solvent with a volume ratio of 5:1, and the dosage of the reaction medium is 20-30 mL.
In the step 4, the solvent is one or more of dichloromethane, chloroform, tetrahydrofuran and dioxane, the drying agent is anhydrous sodium sulfate, the chromatographic column is a 200-mesh 300-mesh silica gel chromatographic column, and the eluent of the chromatographic column is an ethyl acetate-methanol mixed solvent with a volume ratio of 5: 2.
In step 4, the solvent is dichloromethane.
In step 4, after the fractional separation by chromatographic column, collecting and evaporating the first-stage product to dryness to obtain a byproduct 2,8- [ 4-pyridine ] -4, 4-difluoro-1, 3,5, 7-tetramethyl-6-bromo-4-bora-3 a,4 a-diaza-s-indapaci, the chemical structural formula of which is shown as formula II:
the synthetic route of the pyridyl BODIPY derivative dye ligand is as follows:
the raw material 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-fluoro-boron dipyrromethene in the invention can be synthesized by reference to literature (J.Bartelmes, A.J.Francis, K.A.El Roz, F.N.Castellano, W.W.Weare, R.D.Sommer, Light-drive Hydrogen Evolution by BODIPY-transformed Cobaloxime Catalysts, Inorg.Chem.2014,53,4527-4534, Wangbai, Limin, Shenzhen and Yokow, a novel pH fluorescent probe, synthesis, structural and spectral property research of Boron Dipyrromethene (BDP) dye substituted by meso-pyridine, inorganic chemistry report, 2008, 24, 1247-1252), and the approximate synthesis method is as follows: dissolving 2, 4-dimethylpyrrole, 4-pyridylaldehyde and trifluoroacetic acid in a dichloromethane solution, adding dichloro-5, 6-dicyano-p-benzoquinone, N-diisopropylethylamine and a boron trifluoride-diethyl ether solution under the protection of helium to react, washing, filtering, extracting, drying, rotary evaporating and separating by a chromatographic column after the reaction is finished to obtain an intermediate product of red powder, then continuously dissolving the intermediate product in the dichloromethane solution, dropwise adding a dichloromethane solution of N-bromosuccinimide, extracting, drying, rotary evaporating and separating by the chromatographic column after the reaction is finished to obtain a dark red powdery raw material, namely 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-fluoroboron dipyrromethene, the yield was about 82%.
After the technical scheme is adopted, the pyridyl BODIPY derivative dye ligand is a novel BODIPY derivative formed by grafting pyridine on 2,6, 8-position of 1,3,5, 7-tetramethyl BODIPY dipyrromethene serving as a core skeleton, namely an organic dye ligand compound 2,6,8- [ 4-pyridine ] -4, 4-difluoro-1, 3,5, 7-tetramethyl-4-bora-3 a,4 a-diaza-s-indacene with photoactivity in a visible light-near infrared region, and has excellent metal coordination capacity and pH sensitivity.
The preparation method of the pyridyl BODIPY derivative dye ligand is simple and easy to control, and has universal adaptability.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of a target compound of the present invention;
FIG. 2 is an ESI-MS spectrum of a target compound of the present invention;
FIG. 3 is a chart of an infrared spectrum of a target compound of the present invention;
FIG. 4 is a nuclear magnetic hydrogen spectrum of a by-product of the present invention;
FIG. 5 is an ESI-MS spectrum of a by-product of the present invention;
FIG. 6 is an infrared spectrum of a by-product of the present invention;
FIG. 7 shows UV-visible absorption spectra and fluorescence emission spectra of a target compound of the present invention in four different solvent systems;
FIG. 8 is a fluorescence emission spectrum of a target compound of the present invention under different acidic conditions;
FIG. 9 is a graph of the UV-VIS absorption spectrum and fluorescence spectrum of a by-product of the present invention in four different solvent systems;
FIG. 10 is a fluorescence emission spectrum of the by-product of the present invention under different acidic conditions;
FIG. 11 shows [ Zn ] formed by the target compound of the present invention and metallic zinc2(target Compound)2(tp)2·2DMF·7H2O]nCrystal structure diagram of the complex.
Detailed Description
In order to further explain the technical solution of the present invention, the present invention is explained in detail by the following specific examples.
Preparation of pyridyl BODIPY derivative dye ligand
Example 1
A preparation method of a pyridyl boron dipyrromethene derivative dye ligand comprises the following steps:
and 4, dissolving the rotary evaporated product with 50mL of dichloromethane, transferring the solution to a separating funnel, adding 50mL of water for extraction, sequentially drying the organic phase obtained by extraction with anhydrous sodium sulfate, filtering, carrying out rotary evaporation and concentration, carrying out sectional separation on the obtained crude product through a 200-mesh and 300-mesh silica gel chromatographic column, respectively collecting and evaporating two sections of orange-red products by using an eluent which is an ethyl acetate-methanol mixed solvent with a volume ratio of 5:2, and finally obtaining two red powders, wherein the second section of product is a target compound (27.0mg) with a chemical structural formula shown in the formula I, the first section of product is a byproduct (25.6mg) with a chemical structural formula shown in the formula II, the yields are 10.8% and 10.2% respectively, and recrystallizing with dichloromethane can obtain an orange-red single crystal of the target compound.
Example 2
A preparation method of a pyridyl boron dipyrromethene derivative dye ligand comprises the following steps:
and 4, dissolving the rotary evaporated product with 50mL of dichloromethane, transferring the solution to a separating funnel, adding 50mL of water for extraction, sequentially drying the organic phase obtained by extraction with anhydrous sodium sulfate, filtering, carrying out rotary evaporation and concentration, carrying out sectional separation on the obtained crude product through a 200-mesh and 300-mesh silica gel chromatographic column, respectively collecting and evaporating two sections of orange-red products by using an eluent which is an ethyl acetate-methanol mixed solvent with a volume ratio of 5:2, and finally obtaining two red powders, wherein the second section of product is a target compound (55.0mg) with a chemical structural formula shown in the formula I, the first section of product is a byproduct (8.2mg) with a chemical structural formula shown in the formula II, the yields are 22.1% and 3.3% respectively, and carrying out recrystallization by using dichloromethane to obtain an orange-red single crystal of the target compound.
Compared with example 1, the amount of 4-pyridineboronic acid used in this example was increased from 139mg to 200mg, the yield of the target compound increased to 22.1%, and the yield of by-products decreased to 3.3%.
Structure representation of dye ligand of di-and pyridyl BODIPY derivative
1. The structural characterization of the target compound is shown in FIGS. 1-3, IR (KBr pellet, cm)-1)：v＝3429(m)、3037(w)、2968(w)、2919(w)、2851(w)、1733(w)、1601(s)、1528(vs)、1454(s)、1395(m)、1312(vs)、1277(m)、1238(s)、1174(vs)、1106(m)、1086(m)、1013(vs)、846(m)、822(m)、768(m)、719(s)、675(w)、581(m)、522(w)、503(w)；1H NMR(CDCl3,500MHz)：δ＝8.85(d,2H)、8.68(s,4H)、7.41(d,2H)、7.12(d,4H)、2.59(s,6H)、1.40(s,6H)；ESI-MS m/z：[M+H]+calcd.forC28H25BF2N5: 480.2172, found: 480.2174. the nuclear magnetic chemical shift peak, the mass spectrum peak and the infrared absorption peak of the target compound are matched with those of the chemical structural formula I.
2. The structural characterization of the by-product is shown in FIGS. 4-6, IR (KBr pellet, cm)-1)：v＝3439(s)、3037(vw)、2963(vw)、2924(w)、2851(vw)、1723(w)、1596(s)、1537(vs)、1463(s)、1400(s)、1356(s)、1317(s)、1272(m)、1238(s)、1184(vs)、1115(m)、1092(m)、1077(m)、1008(s)、920(w)、826(m)、822(m)、763(m)、719(s)、665(w)、587(w)、567(m)、513(w)；1H NMR(CDCl3,500MHz)：δ＝8.85(d,2H)、8.67(d,2H)、7.35(d,2H)、7.13(d,2H)、2.67(s,3H)、2.57(s,3H)、1.45(s,3H)、1.38(s,3H)；ESI-MS m/z：[M+H]+calcd.for C23H20BF2N4Br: 481.1011, found: 481.1013. the nuclear magnetic chemical shift peak, the mass spectrum peak and the infrared absorption peak of the by-product are matched with the chemical structural formula II.
Photoactive and metal coordinating capability of tri-and pyridyl BODIPY derivative dye ligands
1. The ultraviolet-visible absorption spectrum and the fluorescence emission spectrum of the target compound in four different solvents are shown in fig. 7, the detailed data are shown in table 1, and the target compound shows the characteristic photophysical characteristics of the BODIPY dye: a sharp absorption peak and a fluorescence emission peak, wherein the intrinsic transition absorption peak appears around 520-524nm, and the intrinsic transition emission peak appears in the range of 552-556nm, the former is attributed to the pi → pi transition of the target compound, and the latter is attributed to the pi → pi transition of the target compound.
TABLE 1 spectral properties of the target compounds in different solvents
Note:aabsorbing light wavelengths;ba wavelength of the emitted light;cmolar extinction coefficient;dquantum yield of light
2. The ultraviolet visible absorption spectrum and the fluorescence emission spectrum of the byproduct in four different solvents are shown in FIG. 9, the detailed data are shown in Table 2, the intrinsic transition ultraviolet visible absorption spectrum and the intrinsic transition fluorescence emission spectrum of the byproduct respectively appear at 515-519nm and 550-556nm, and compared with the target compound, the ultraviolet visible absorption spectrum of the byproduct shows an obvious blue shift phenomenon, which is the embodiment of the difference of the photophysical properties generated after the substitution of the electron-withdrawing group Br and the electron-pushing functional group pyridine, and reflects that the target compound has the characteristic of a reddish absorption spectrum compared with the byproduct.
TABLE 2 spectral properties of the by-products in different solvents
Note:aabsorbing light wavelengths;ba wavelength of the emitted light;cmolar extinction coefficient;dquantum yield of light
3. The fluorescence spectra of the target compound and the by-product in the acidic medium are shown in fig. 8 and 10, and both have good pH sensitivity in the acidic medium, exhibit corresponding fluorescence intensity response to different pH values, and can be used as an effective pH probe.
4. The target compound has good metal coordination capability and forms [ Zn ] with metallic zinc2(target Compound)2(tp)2·2DMF·7H2O]nThe crystal structure of the complex is shown in FIG. 11.
The above embodiments and drawings are not intended to limit the form and style of the present invention, and any suitable changes or modifications thereof by those skilled in the art should be considered as not departing from the scope of the present invention.
Claims (10)
1. A pyridyl-boron dipyrromethene derivative dye ligand, which is characterized in that: the chemical structural formula is shown as a formula I,
is named 2,6,8- [ 4-pyridine ] -4, 4-difluoro-1, 3,5, 7-tetramethyl-4-bora-3 a,4 a-diaza-s-indacene.
2. The process for preparing a pyridylfluorodipyrromethene derivative dye ligand according to claim 1, wherein: the method comprises the following steps:
step 1, putting 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-boron dipyrromethene and 4-pyridine boric acid into a reaction container, and adding alkali and a palladium catalyst;
step 2, adding a reaction medium into a protective gas atmosphere, controlling the reaction temperature to be 25-95 ℃ under the stirring condition, and reacting for 8-24 hours;
step 3, after the thin-layer chromatography detects that the reactants are completely consumed, carrying out suction filtration on the reaction liquid, and carrying out rotary evaporation on the filtrate obtained by suction filtration;
and 4, dissolving the rotary-evaporated product by using a small amount of solvent, adding water for extraction, drying the organic phase obtained by extraction by using a drying agent, filtering, carrying out rotary evaporation concentration, carrying out sectional separation by using a chromatographic column, collecting and evaporating a second-stage product by distillation, and finally obtaining the target compound, namely the pyridyl boron dipyrromethene derivative dye ligand.
3. The method for preparing a pyridyl-boron dipyrromethene derivative dye ligand according to claim 2, wherein: in the step 1, the chemical structural formula of the 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-boron dipyrromethene is as follows:
the chemical structural formula of the 4-pyridine boric acid is as follows:
4. the method for preparing a pyridyl-boron dipyrromethene derivative dye ligand according to claim 2, wherein: in the step 1, the alkali is one or two of potassium carbonate and sodium carbonate, and the palladium catalyst is one or two of [1,1' -bis (diphenylphosphino) ferrocene ] -palladium dichloride catalyst and [ tetrakis (triphenylphosphine) ] palladium catalyst; the molar ratio of the 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-fluoroboron dipyrromethene to the 4-pyridine boric acid to the alkali to the palladium catalyst is 0.50-1.00: 1.10-3.20: 1.40-2.80: 0.05-0.10.
5. The method for preparing a pyridyl-boron dipyrromethene derivative dye ligand according to claim 4, wherein: in the step 1, the molar ratio of the 8- [ 4-pyridine ] -1,3,5, 7-tetramethyl-2, 6-dibromo-fluoroboron dipyrromethene to the 4-pyridine boric acid to the base to the palladium catalyst is 0.52:1.13:1.45: 0.05.
6. The method for preparing a pyridyl-boron dipyrromethene derivative dye ligand according to claim 2, wherein: in the step 2, the protective gas is one of nitrogen, helium and argon, the reaction medium is one or more of water, dichloromethane, trichloromethane, tetrahydrofuran, dioxane, acetonitrile, DMF, toluene, ethyl acetate, n-hexane, petroleum ether, methanol, ethanol and isopropanol, the reaction temperature is 80 ℃, and the reaction time is 14 h.
7. The method for preparing a pyridyl-BODIPY derivative dye ligand according to claim 6, wherein the method comprises the following steps: in the step 2, the reaction medium is a dioxane-water mixed solvent with a volume ratio of 5:1, and the dosage of the reaction medium is 20-30 mL.
8. The method for preparing a pyridyl-boron dipyrromethene derivative dye ligand according to claim 2, wherein: in the step 4, the solvent is one or more of dichloromethane, chloroform, tetrahydrofuran and dioxane, the drying agent is anhydrous sodium sulfate, the chromatographic column is a 200-mesh 300-mesh silica gel chromatographic column, and the eluent of the chromatographic column is an ethyl acetate-methanol mixed solvent with a volume ratio of 5: 2.
9. The method for preparing a pyridyl-boron dipyrromethene derivative dye ligand according to claim 8, wherein: in step 4, the solvent is dichloromethane.
10. The method for preparing a pyridyl-boron dipyrromethene derivative dye ligand according to claim 2, wherein: in step 4, after the fractional separation by chromatographic column, collecting and evaporating the first-stage product to dryness to obtain a byproduct 2,8- [ 4-pyridine ] -4, 4-difluoro-1, 3,5, 7-tetramethyl-6-bromo-4-bora-3 a,4 a-diaza-s-indapaci, the chemical structural formula of which is shown as formula II:
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